You have to put "cheap out" into context. They still have a top 10 payroll. They are not going to spend like the Dodgers, Mets or Phillies and quite frankly, that's ridiculous to have that expectation. The Dodgers ownership setup is far more lucrative than any other team in baseball. It's play money.They don’t have to spend like the Mets but they should be over the tax threshold 2 of 3 years. If they did, they’d own the division. As it stands, they can’t beat the Brewers and that won’t change if they cheap out the way they have been.
TO A POINT, A VERY SMALL POINT, Ricketts' commentary about Wrigley is true. There is maintenance associated with it that no other team has to deal with and amongst the top tier spenders, Wrigley is smaller. The Dodgers and Yankees can pack in 50,000+ people. Not sure about the Phillies. So, the Cubs have roughly 3M come through the gates, which is top 10. That said, the Cubs ticket prices are ridiculous, everything sold in the stadium is ridiculous and there's a crazy amount of revenue stream that comes in from outside of the stadium due to Wrigley. It's that portion that I'm not sure Ricketts considers being part of baseball operations. To that family, the Cubs are just one of many business units that they manage to the bottom line. It's a separate entity from other parts of their fortune. It's a tentacle from the mother ship per se.
You made a comment, and a darn good one, about not being able to best the Brewers. That's occurring despite the Cubs spending a LOT more on the major league club. That should never happen and that fact that it does is really on Hoyer. Ricketts gives him a budget of "xyz" and it's Hoyer's job and the developmental guys at the lower levels jobs to make the pieces fit. The Brewers lose all stars to free agency and just replace them with developed talent in the minors. The Cubs aren't able to go into their farm system and plug and play. VERY rarely has that occurred over the years, especially with pitching. That's not a Ricketts issue. If he's handing over $240M, that is PLENTY to win that division literally every year.
It's dueling issues that lead to unacceptable outcomes over the years. The World Series winner was a decade ago now. The grace period is over.
All that said, I'm not sure what the looming strike/lockout, which could last all season next year into the season after, is doing with regards to decision making with all of the teams. Baseball needs a huge fix from a structural/competitive standpoint which is going to have to include some sort of cap and maybe a salary floor. The players union won't budge, nor will the owners. So, not sure where that fits into everything.